US6187509B1ExpiredUtility

Positive type electrodeposition photoresist compositions and pattern formation process

Assignee: KANSAI PAINT CO LTDPriority: Oct 7, 1997Filed: Oct 7, 1998Granted: Feb 13, 2001

Est. expiryOct 7, 2017(expired)· nominal 20-yr term from priority

Inventors:Genji Imai Hideo Kogure Takeya Hasegawa

G03F 7/168G03F 7/164G03F 7/039G03F 7/0045G03F 7/0236G03F 7/0392C08F 290/062G03F 7/0757G03F 7/0233G03F 7/0397G03F 7/0395

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Claims

Abstract

A positive type electrodeposition photoresist composition characterized by neutralizing by a basic compound and dissolving or dispersing in an aqueous medium a composition comprising (A) a polymer having 0.5-10 equivalents of carboxyl group(s) and optionally having more than 1 equivalent of hydroxyphenyl group(s) per kg polymer, or (A′) a polymer having 0.5-10 equivalents of carboxyl group(s) per kg polymer and (A″) a polymer having more than 1 equivalent of hydroxyphenyl group(s) per kg polymer; (B) a compound having at least two vinyl ether groups per molecule; (C) a compound which generates an acid when irradiated with a visible light; and (D) a sensitizing dye, and a process for pattern formation using such a composition are disclosed. Said composition has excellent thermal stability, high resolution and formability of fine image pattern and is useful to positive type photoresist, printing material etc.

Claims

exact text as granted — not AI-modified

What is claimed is:  
     
       1. A positive-type electrodeposition photoresist composition which comprises a solution or dispersion obtained by neutralizing with a basic compound, a composition comprising (A) a polymer having 0.5-10 equivalents of carboxyl group(s) and optionally having more than 1 equivalent of hydroxyphenyl group(s) per kg polymer; (B) a compound having at least two vinyl ether groups per molecule; (C) a compound which generates an acid when irradiated with a visible light, represented by the general formula                    
       wherein R represents                    
       group (where R 1 , R 2  and R 3  each independently represent hydrogen atom or fluorine atom),                    
       and (D) a sensitizing dye, and dissolving or dispersing the composition in an aqueous medium. 
     
     
       2. The composition set forth in claim  1 , wherein the polymer (A) has a number-average molecular weight of about 500 to about 100,000. 
     
     
       3. The composition set forth in claim  1 , wherein the polymer (A) has carboxyl group(s) of 0.5-8 equivalents per kg of the polymer. 
     
     
       4. The composition set forth in claim  1 , wherein the polymer (A) has hydroxyphenyl group(s) of 1-10 equivalents per kg of the polymer. 
     
     
       5. The composition set forth in claim  1 , wherein the polymer (A) has a glass transition temperature (Tg) not lower than 0° C. 
     
     
       6. The composition set forth in claim  1 , which contains the vinyl ether group-containing compound (B) in an amount of 5-150 parts by weight per 100 parts per weight of the polymer (A). 
     
     
       7. The composition set forth in claim  1 , which contains the photochemically-acid-generating compound (C) in an amount of 0.1-40 parts by weight per 100 parts by weight of the total of the polymer (A) and the vinyl ether group-containing compound (B). 
     
     
       8. The composition set forth in claim  1 , which contains the sensitizing dye (D) in an amount of 0.1-10 parts by weight per 100 parts by weight of the total of the polymer (A) and the vinyl ether group-containing compound (B). 
     
     
       9. A positive-type electrodeposition photoresist composition which comprises a solution or dispersion obtained by neutralizing with a basic compound, a composition comprising (A′) a polymer having 0.5-10 equivalents of carboxyl group(s) per kg polymer; (A″) a polymer having more than 1 equivalent of hydroxyphenyl group(s) per kg polymer; (B) a compound having at least two vinyl ether groups per molecule; (C) a compound which generates an acid when irradiated with a visible light, represented by the general formula                    
       wherein R represents                    
       group (where R 1 , R 2  and R 3  each independently represent hydrogen atom or fluorine atom),                    
       and (D) a sensitizing 
       dye, and dissolving or dispersing the composition in an aqueous medium.  
     
     
       10. The composition set forth in claim  9 , wherein the polymer (A′) has a number-average molecular weight of about 3,000 to about 100,000. 
     
     
       11. The composition set forth in claim  9 , wherein the polymer (A′ ) has carboxyl group(s) of 0.5-8 equivalents per kg of the polymer. 
     
     
       12. The composition set forth in claim  9 , wherein the polymer (A″) has a number-average molecular weight of about 500 to about 100,000. 
     
     
       13. The composition set forth in claim  9 , wherein the polymer (A″) has hydroxyphenyl group(s) of 1-10 equivalents per kg of the polymer. 
     
     
       14. The composition set forth in claim  9 , wherein each of the polymers (A′) and (A″) has a glass transition temperature (Tg) not lower than 0° C. 
     
     
       15. The composition set forth in claim  9 , wherein the proportion by weight of the polymer (A′) and the polymer (A″) is 90/10-10/90. 
     
     
       16. The composition set forth in claim  9 , which contains the vinyl ether group-containing compound (B) in an amount of 5-150 parts by weight per 100 parts by weight of the total of the polymer (A′) and the polymer (A″). 
     
     
       17. The composition set forth in claim  9 , which contains the photochemically-acid-generating compound (C) in an amount of 0.1-40 parts by weight per 100 parts by weight of the total of the polymer (A′), the polymer (A″) and the vinyl ether group-containing compound (B). 
     
     
       18. The composition set forth in claim  9 , which contains the sensitizing dye (D) in an amount of 0.1-10 parts by weight per 100 parts by weight of the total of the polymer (A′), the polymer (A″) and the vinyl ether group-containing compound (B). 
     
     
       19. The composition set forth in claim  1  or claim  9 , wherein the vinyl ether group-containing compound (B) is a low-molecular weight or high-molecular weight compound having, in the molecule, two to four vinyl ether groups represented by a formula —R′—O—CH═CH 2 , wherein R′ represents a C 1 -C 6  straight chain or branched chain alkylene group. 
     
     
       20. The composition set forth in claim  1  or claim  9 , wherein the vinyl ether group-containing compound (B) is a condensation product between a polyphenol compound and a halogenated alkyl vinyl ether, or a reaction product between a polyisocyanate compound having an aromatic ring and a hydroxyalkyl vinyl ether. 
     
     
       21. The composition set forth in claim  1  or claim  9 , wherein the photochemically-acid-generating compound (C) is selected from the group consisting of                    
     
     
       22. The composition set forth in claim  1  or claim  9 , wherein the sensitizing dye (D) is selected from the group consisting of compounds represented by general formulae                    
       wherein R 4 , R 5 , R 6  and R 7  each independently represents methyl, ethyl, propyl or isopropyl groups, and R 8  and R 9  each independently represents hydrogen atom, alkyl group of 1-4 carbon atoms, alkoxy group of 1-4 carbon atoms, alkoxycarbonyl group of 2-5 carbon atoms, dialkylamino group of 1-4 carbon atoms in each alkyl moiety, Cl, Br, CN, NO 2  or SO 2 CH 3 ; and                    
       wherein R 10 , R 11  and R 12  each independently represents methyl, ethyl, propyl or isopropyl groups, and R 13  and R 14  each independently represents hydrogen atom, alkyl group of 1-4 carbon atoms, alkoxy group of 1-4 carbon atoms, alkoxycarbonyl group of 2-5 carbon atoms, dialkylamino group of 1-4 carbon atoms in each alkyl moiety, Cl, Br, CN, NO 2  or SO 2 CH 3 ; cyanine dyes, merocyanine dyes and coumarin dyes.  
     
     
       23. The composition set forth in claim  1  or claim  9 , which further contains hydrophilic resins. 
     
     
       24. The composition set forth in claim  1  or claim  9  wherein the composition is neutralized with a basic compound in an amount of 0.1-1 equivalent per carboxyl group in the polymer (A) or (A′). 
     
     
       25. A process for pattern formation which comprises conducting sequentially: a step of coating a positive type electrodeposition photoresist composition as set forth in claim  1  or claim  9  on a substrate having an electroconductive surface by electrodeposition; a step of heating said substrate; a step of irradiating the resulting substrate image-selectively with a visible light; a step of heating the irradiated substrate, and a step of subjecting the resulting substrate to development with a basic developer. 
     
     
       26. The process for pattern formation set forth in claim  25 , which further comprises a step of contacting the substrate with water, after the step of irradiating the substrate image-selectively with a visible light. 
     
     
       27. A pattern which is formed by the process set forth in claim  25 . 
     
     
       28. A pattern which is formed by the process set forth in claim  26 .

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